Triethylamine → HCID 54429599, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-fluorobenzoic acid (4.5 g, 32.14 mmol), oxalyl chloride (4.1 mL, 48.2 mL), DMF (2 drops) and methylene chloride (40 mL) was heated 2 hours at reflux. The reaction mixture was allowed to cool to 25° C., then stirred approximately 12 hours and concentrated. The residue was slowly added to a suspension of 2-bromoethylamine hydrobromide (5.7 g, 28 mmol), triethylamine (21 mL, 160 mmol) and benzene (200 mL). The mixture was heated 12 hours at reflux, allowed to cool to 25° C., stirred an additional 12 hours and diluted with water. The aqueous layer was separated and extracted with methylene chloride (2×50 mL). The combined extracts were dried (MgSO4) and concentrated. The residue was purified on silica gel by column chromatography eluting with hexanes/ethyl acetate (5:1) to give 2-fluoro-1-(4,5-dihydrooxazol-2-yl)benzene (1.96 g, 11.9 mmol).

Provenance & Evidence